I have a mould solution that I intend to treat a futon mattress with. The active ingredient is 2.4g/L sodium hydroxide, 1.2g/L alkaline salts and 42g/L of sodium hypochlorite. Will this formula damage the fibre of the futon cover so that I will need to apply deactivating agent post treatment? What would I require for this?

Riff-in-Thyme said:

I have a mould solution that I intend to treat a futon mattress with. The active ingredient is 2.4g/L sodium hydroxide, 1.2g/L alkaline salts and 42g/L of sodium hypochlorite. Will this formula damage the fibre of the futon cover so that I will need to apply deactivating agent post treatment? What would I require for this?

The only problem I can see is bleaching if it’s coloured. Vinegar would go a long way in neutralising if necessary.

jjjust moi said:

Riff-in-Thyme said:

I have a mould solution that I intend to treat a futon mattress with. The active ingredient is 2.4g/L sodium hydroxide, 1.2g/L alkaline salts and 42g/L of sodium hypochlorite. Will this formula damage the fibre of the futon cover so that I will need to apply deactivating agent post treatment? What would I require for this?

The only problem I can see is bleaching if it’s coloured. Vinegar would go a long way in neutralising if necessary.

Aah of course. I’d only come up with using fish tank neutraliser as an idea.

Riff-in-Thyme said:

I have a mould solution that I intend to treat a futon mattress with. The active ingredient is 2.4g/L sodium hydroxide, 1.2g/L alkaline salts and 42g/L of sodium hypochlorite. Will this formula damage the fibre of the futon cover so that I will need to apply deactivating agent post treatment? What would I require for this?

Sodium hypochlorite can react with certain organics. What’s your futon cover made out of?

mine is all cotton. cover and innards.

Twoy said:

Sodium hypochlorite can react with certain organics. What’s your futon cover made out of?

Cotton

Riff-in-Thyme said:

Twoy said:

Sodium hypochlorite can react with certain organics. What’s your futon cover made out of?

Cotton

That will be fine. I have some vague understanding that bleach has a detrimental effect on some of the artificial polymer fibres but it shouldn’t hurt cotton at all.

Twoy said:

Riff-in-Thyme said:

Twoy said:

Sodium hypochlorite can react with certain organics. What’s your futon cover made out of?

Cotton

That will be fine. I have some vague understanding that bleach has a detrimental effect on some of the artificial polymer fibres but it shouldn’t hurt cotton at all.

That is great. Thanks Twoy.

This is as good a place as any to ask this question:

Does the acetate ion exhibit the haloform reaction? The haloform reaction is the reaction between a halogen and a methyl ketone (or the corresponding alcohol) under basic conditions to produce the corresponding haloform. For example, acetone reacts with hypochlorite ion to form chloroform, and reaction with iodine under basic conditions to form bright yellow crystals of iodoform is a test for methyl ketones or the corresponding alcohols. I’ve never heard of being applicable to acetate, but acetate does qualitatively satisfy the requirements of a methyl ketone from a reaction mechanistic perspective (though perhaps not quantitatively).

KJW said:

This is as good a place as any to ask this question:

Does the acetate ion exhibit the haloform reaction? The haloform reaction is the reaction between a halogen and a methyl ketone (or the corresponding alcohol) under basic conditions to produce the corresponding haloform. For example, acetone reacts with hypochlorite ion to form chloroform, and reaction with iodine under basic conditions to form bright yellow crystals of iodoform is a test for methyl ketones or the corresponding alcohols. I’ve never heard of being applicable to acetate, but acetate does qualitatively satisfy the requirements of a methyl ketone from a reaction mechanistic perspective (though perhaps not quantitatively).

I didn’t know that

handy to know if you were in some post apocalyptic situation and needed to make anaesthetic for operations etc

if you were in a post apocalyptic world

how would the amateur make anti biotics?

I’ve heard of mould on oranges (ITD)

if you were to manufacture antibiotics from scratch in some day after tomorrow situation, I guess you’d need a microscope and know how to identify good stuff from bad stuff

you’d need to be able to sterilise some dishes to grow the mould

you might cultivate and store lots of penicillin dust to sprinkle over wounds after you had performed surgery in less than sterile surrounds?

strangely enough they never mentioned this method to make chloroform at school

there would be too many teachers falling victim to pranksters

wookiemeister said:

KJW said:

This is as good a place as any to ask this question:

Does the acetate ion exhibit the haloform reaction? The haloform reaction is the reaction between a halogen and a methyl ketone (or the corresponding alcohol) under basic conditions to produce the corresponding haloform. For example, acetone reacts with hypochlorite ion to form chloroform, and reaction with iodine under basic conditions to form bright yellow crystals of iodoform is a test for methyl ketones or the corresponding alcohols. I’ve never heard of being applicable to acetate, but acetate does qualitatively satisfy the requirements of a methyl ketone from a reaction mechanistic perspective (though perhaps not quantitatively).

I didn’t know that

handy to know if you were in some post apocalyptic situation and needed to make anaesthetic for operations etc

It seems from Wikipedia that acetate does not react, as it explicitly mentions ethanol and ethanal in addition to the methyl ketones and their corresponding alcohols, but not acetate. I do see the relatively high pK_a of the a-proton as an obstacle to the reaction, in addition to the possible stability of trichloroacetate under basic conditions (I found no mention that trichloroacetate decomposes to chloroform in the presence of aqueous hydroxide). It is worth mentioning that chloral (or chloral hydrate) is quite stable under neutral or acidic conditions, but does decompose to chloroform in the presence of aqueous hydroxide.

KJW said:

wookiemeister said:

KJW said:

This is as good a place as any to ask this question:

Does the acetate ion exhibit the haloform reaction? The haloform reaction is the reaction between a halogen and a methyl ketone (or the corresponding alcohol) under basic conditions to produce the corresponding haloform. For example, acetone reacts with hypochlorite ion to form chloroform, and reaction with iodine under basic conditions to form bright yellow crystals of iodoform is a test for methyl ketones or the corresponding alcohols. I’ve never heard of being applicable to acetate, but acetate does qualitatively satisfy the requirements of a methyl ketone from a reaction mechanistic perspective (though perhaps not quantitatively).

I didn’t know that

handy to know if you were in some post apocalyptic situation and needed to make anaesthetic for operations etc

It seems from Wikipedia that acetate does not react, as it explicitly mentions ethanol and ethanal in addition to the methyl ketones and their corresponding alcohols, but not acetate. I do see the relatively high pK_a of the a-proton as an obstacle to the reaction, in addition to the possible stability of trichloroacetate under basic conditions (I found no mention that trichloroacetate decomposes to chloroform in the presence of aqueous hydroxide). It is worth mentioning that chloral (or chloral hydrate) is quite stable under neutral or acidic conditions, but does decompose to chloroform in the presence of aqueous hydroxide.

are you trying to make something?

I don’t know enough about this reaction to give much information

hang on

it kind of reminds me of esters a little where you can cook up an acetate with an alcohol

the chloroform must bubble off as a gas from the mixture

no its a liquid separate from the other stuff

http://www.digitalprecursor.org/showthread.php/245-Synthesis-of-Chloroform-using-Na-Hypochlorite-(w-pix)

wookiemeister said:

are you trying to make something?

I don’t know enough about this reaction to give much information

The relevance to this thread is the earlier suggestion that vinegar be used to neutralise a mixture of hypochlorite and hydroxide. Also, someone (IRL) once asked me if it’s safe to mix bleach with vinegar. While it’s generally not safe to mix bleach with anything, I could see no particular reason why one shouldn’t mix bleach with vinegar, except the generation of gaseous chlorine under the acidic conditions. But then I thought about the possibility of the haloform reaction (even though it is not a methyl ketone or oxidisable to such).

KJW said:

wookiemeister said:

are you trying to make something?

I don’t know enough about this reaction to give much information

The relevance to this thread is the earlier suggestion that vinegar be used to neutralise a mixture of hypochlorite and hydroxide. Also, someone (IRL) once asked me if it’s safe to mix bleach with vinegar. While it’s generally not safe to mix bleach with anything, I could see no particular reason why one shouldn’t mix bleach with vinegar, except the generation of gaseous chlorine under the acidic conditions. But then I thought about the possibility of the haloform reaction (even though it is not a methyl ketone or oxidisable to such).

I’ve seen HCL been mixed with a strong solution of hypochlorite (being done unintentionally), I jumped out of the area when I realised what they had stupidly done

as far as i’m aware its totally legal to make chloroform

At a previous workplace, the chemist in charge (chemical engineer) mixed dry hypochlorite into general treated waste. The neighbouring businesses saw the resultant smoke and called the firies.

Riff-in-Thyme said:

I have a mould solution that I intend to treat a futon mattress with. The active ingredient is 2.4g/L sodium hydroxide, 1.2g/L alkaline salts and 42g/L of sodium hypochlorite. Will this formula damage the fibre of the futon cover so that I will need to apply deactivating agent post treatment? What would I require for this?

is this mould solution home made?

if its been bought you should ring the manufacturer and ask them

I used to have a futon but found that they tend to get hard over time

recently I’ve just moved it outside for the dogs to lay on during the day

its really the bed of the single male with no GF. women as a general rule don’t like sleeping on them

wookiemeister said:

Riff-in-Thyme said:

I have a mould solution that I intend to treat a futon mattress with. The active ingredient is 2.4g/L sodium hydroxide, 1.2g/L alkaline salts and 42g/L of sodium hypochlorite. Will this formula damage the fibre of the futon cover so that I will need to apply deactivating agent post treatment? What would I require for this?

is this mould solution home made?

if its been bought you should ring the manufacturer and ask them

I used to have a futon but found that they tend to get hard over time

recently I’ve just moved it outside for the dogs to lay on during the day

its really the bed of the single male with no GF. women as a general rule don’t like sleeping on them

noted. The futon is for a couch arrangement for the resident animal. I will find something to condition it with to keep it from going stiff.

Riff-in-Thyme said:

wookiemeister said:

Riff-in-Thyme said:

I have a mould solution that I intend to treat a futon mattress with. The active ingredient is 2.4g/L sodium hydroxide, 1.2g/L alkaline salts and 42g/L of sodium hypochlorite. Will this formula damage the fibre of the futon cover so that I will need to apply deactivating agent post treatment? What would I require for this?

is this mould solution home made?

if its been bought you should ring the manufacturer and ask them

I used to have a futon but found that they tend to get hard over time

recently I’ve just moved it outside for the dogs to lay on during the day

its really the bed of the single male with no GF. women as a general rule don’t like sleeping on them

noted. The futon is for a couch arrangement for the resident animal. I will find something to condition it with to keep it from going stiff.

you could always throw a towel over it and just wash the towel periodically

Sodium Thiosulfate is used to murder Sodium Hypochlorite in water treatment, but I don’t know how it achieves it.

Have you tried contacting the anti-mould chemical manufacturer? I suspect it would be just a matter of rinsing until it’s all gone.

ps – Wear gloves. I burnt the shit out of my hands de-moulding a canvas tent with that stuff.

>It seems from Wikipedia that acetate does not react, as it explicitly mentions ethanol and ethanal in addition to the methyl ketones and their corresponding alcohols, but not acetate. I do see the relatively high pKa of the a-proton as an obstacle to the reaction, in addition to the possible stability of trichloroacetate under basic conditions (I found no mention that trichloroacetate decomposes to chloroform in the presence of aqueous hydroxide). It is worth mentioning that chloral (or chloral hydrate) is quite stable under neutral or acidic conditions, but does decompose to chloroform in the presence of aqueous hydroxide.

acetate is a product of the haloform reaction on acetone. That fact alone excludes it as a reactant.

morrie said:

acetate is a product of the haloform reaction on acetone. That fact alone excludes it as a reactant.

So acetone doesn’t react on both sides of the carbonyl group?

KJW said:

morrie said:

acetate is a product of the haloform reaction on acetone. That fact alone excludes it as a reactant.

So acetone doesn’t react on both sides of the carbonyl group?

No, acetone doesn’t. Once the first chlorine replaces a hydrogen, the others substitute on the same side, as the already chlorinated carbon is more susceptible to further chlorination.

Once acetate is formed, there is no longer a carbonyl group, as the two oxygens are resonance stabilized, so that they are equivalent, but are not the same as the original carbonyl group in the acetone.

morrie said:

KJW said:

morrie said:

acetate is a product of the haloform reaction on acetone. That fact alone excludes it as a reactant.

So acetone doesn’t react on both sides of the carbonyl group?

No, acetone doesn’t. Once the first chlorine replaces a hydrogen, the others substitute on the same side, as the already chlorinated carbon is more susceptible to further chlorination.

This doesn’t actually prevent chlorination on both sides, It just means that one side will fully chlorinate before the other. The inductive effect of the trichloromethyl group will enhance acidity and hence reactivity on the other side of the carbonyl group.

I looked up the reaction between acetone and calcium hypochlorite (a method for preparing chloroform) in an old pharmaceutical chemistry book I have, and it does say that calcium acetate is the main other product, though it also said that some hexachloroacetone is probably also produced, leading to calcium carbonate (I don’t know why the book wasn’t certain about this).

morrie said:

Once acetate is formed, there is no longer a carbonyl group, as the two oxygens are resonance stabilized, so that they are equivalent, but are not the same as the original carbonyl group in the acetone.

I’m aware that ketones and carboxylic acids are different functional groups, but the carboxyl group does enhance the acidity of the a-protons, just as a carbonyl group does, though to a lesser degree (eg in the Claisen condensation). Admittedly, the negative charge already on the carboxylate will dissuade deprotonation at the a-carbon. So, even if acetate ions don’t significantly react with hypochlorite, maybe acetate esters do (if they don’t saponify first)?

KJW said:

I looked up the reaction between acetone and calcium hypochlorite (a method for preparing chloroform) in an old pharmaceutical chemistry book I have, and it does say that calcium acetate is the main other product, though it also said that some hexachloroacetone is probably also produced, leading to calcium carbonate (I don’t know why the book wasn’t certain about this).

Even if calcium acetate does react with calcium hypochlorite, one would expect the reaction to be much slower than with acetone, so if one sets up the stoichiometry to produce calcium acetate, then calcium acetate would be produced in good yield. Thus, the predominant formation of calcium acetate doesn’t establish that calcium acetate doesn’t react, only that its reaction is much slower.

morrie said:

the already chlorinated carbon is more susceptible to further chlorination.

Does this mean that some carbon tetrachloride is also produced in the haloform reaction with hypochlorite?

Cl₃CH + ^–OH —› Cl₃C^– + HOH
Cl₃C^– + ClO^– + HOH —› CCl₄ + 2 ^–OH

or alternatively

Cl₃CH + ^–OH —› Cl₂C: + Cl^– + HOH
Cl^– + ClO^– + HOH —› Cl₂ + 2 ^–OH
Cl₂C: + Cl₂ —› CCl₄

KJW said:

KJW said:

I looked up the reaction between acetone and calcium hypochlorite (a method for preparing chloroform) in an old pharmaceutical chemistry book I have, and it does say that calcium acetate is the main other product, though it also said that some hexachloroacetone is probably also produced, leading to calcium carbonate (I don’t know why the book wasn’t certain about this).

Even if calcium acetate does react with calcium hypochlorite, one would expect the reaction to be much slower than with acetone, so if one sets up the stoichiometry to produce calcium acetate, then calcium acetate would be produced in good yield. Thus, the predominant formation of calcium acetate doesn’t establish that calcium acetate doesn’t react, only that its reaction is much slower.

The thing is that hydroxide if formed in the first step and once the first trichloride is formed it reacts with the hydroxide. That is the beauty of the reaction. Even if you overdid the hypochlorite, I think that the reaction with the hydroxide is going to be favoured in terms of kinetics, so you will get to the acetate before further chlorination of the acetone.

That said, there is probably some minor reaction leading to the carbonate. Very few organic reactions are without some minor by-product.

KJW said:

morrie said:

the already chlorinated carbon is more susceptible to further chlorination.

Does this mean that some carbon tetrachloride is also produced in the haloform reaction with hypochlorite?

Cl₃CH + ^–OH —› Cl₃C^– + HOH
Cl₃C^– + ClO^– + HOH —› CCl₄ + 2 ^–OH

or alternatively

Cl₃CH + ^–OH —› Cl₂C: + Cl^– + HOH
Cl^– + ClO^– + HOH —› Cl₂ + 2 ^–OH
Cl₂C: + Cl₂ —› CCl₄

It is my recollection that chloroform is pretty unstable in any event so there are lots of possibilities. IIRC carbon tet. is a possible degradation product. Makes you think twice about experimenting with chloroform.

morrie said:

KJW said:

morrie said:

the already chlorinated carbon is more susceptible to further chlorination.

Does this mean that some carbon tetrachloride is also produced in the haloform reaction with hypochlorite?

Cl₃CH + ^–OH —› Cl₃C^– + HOH
Cl₃C^– + ClO^– + HOH —› CCl₄ + 2 ^–OH

or alternatively

Cl₃CH + ^–OH —› Cl₂C: + Cl^– + HOH
Cl^– + ClO^– + HOH —› Cl₂ + 2 ^–OH
Cl₂C: + Cl₂ —› CCl₄

It is my recollection that chloroform is pretty unstable in any event so there are lots of possibilities. IIRC carbon tet. is a possible degradation product. Makes you think twice about experimenting with chloroform.

my lungs regret many experiments.

morrie said:

I think that the reaction with the hydroxide is going to be favoured in terms of kinetics, so you will get to the acetate before further chlorination of the acetone.

I was actually considering addressing this point in my earlier post because I assume this to be the rate-determining step. However, the extent of chlorination of acetone is a side-issue to the original question about whether acetate reacts with hypochlorite. There is one mechanism worth considering:

CH₃(CO)–O^– + ClO^– + HOH —› CH₃(CO)–OCl + 2 ^–OH (I’ve labelled the oxygen to differentiate between two distinct mechanisms)
CH₃(CO)–OCl —› —› —› CCl₃(CO)–OCl
etc

Here, it is acetyl hypochlorite rather than acetate itself that is being chlorinated, the hypochlorite ester activating the a-carbon to deprotonation and eventual chlorination.